B-Bromo- or B-iodo-9-borabicyclo[3.3.1]nonane (B-X-9-BBN) and other haloboranes such as BBr3 react readily with 1-alkynes through Markovnikov cis-addition of the X-B moiety to C≡C bonds. The haloboration occurs chemoselectively at terminal C≡C bonds, but not at internal C≡C, or terminal and internal C=C bonds. The haloboration adducts thus obtained are valuable intermediates to provide various organic compounds stereo- and regioselectively in good yields. In this paper, the authors review synthetic applications of the haloboration reaction, mostly carried out in their laboratory.
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